Sulfuric Acid → 2-Propenoic acid, 3-(4-methoxyphenyl)-, 2-ethylhexyl ester

HRID 2379303Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](N)=[CH:5][CH:4]=1.S(=O)(=O)(O)O.C(C(CCCC)CO)C.N(OCCCCC)=O.[C:32]([O:36][CH2:37][CH:38]([CH2:43][CH3:44])[CH2:39][CH2:40][CH2:41][CH3:42])(=[O:35])[CH:33]=[CH2:34]>O.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:34]=[CH:33][C:32]([O:36][CH2:37][CH:38]([CH2:43][CH3:44])[CH2:39][CH2:40][CH2:41][CH3:42])=[O:35])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 10 °C

Procedure

12.3 g of 4-anisidine (4-methoxyaniline) are mixed while stirring with 10 ml of concentrated sulphuric acid and 60 ml of 2-ethylhexanol and the mixture is cooled to about 10° C. Subsequently 11.7 g of amyl nitrite are added and after addition is complete the mixture is stirred for a further 40 minutes. The reaction mixture is subsequently admixed with 20.2 g of 2-ethylhexyl acrylate and 100 mg of Pd (5% Pd on activated carbon) and heated to 65° C. over a period of 1 hour and stirred for a further 12 hours at this temperature. The mixture is diluted with 100 ml of water and extracted with 200 ml of dichloromethane. As examination by thin-layer chromatography and gas chromatography shows, 2-ethylhexyl p-methoxycinnamate has not been formed in even the smallest amounts. The 2-ethylhexyl acrylate employed is essentially present in unchanged form.

Workup

additionafter addition
temperatureheated to 65° C. over a period of 1 hour
stirringstirred for a further 12 hours at this temperature
extractionextracted with 200 ml of dichloromethane

Sources & evidence

ORD record: ord-fde3cb6e344247e3ab2f5d8362bd2305
Source dataset: uspto-grants-1994_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05360924

Reaction notes

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